Tatheelrod -
1) I suspect that the reason that the teak is riding up on the screw is because the hole in the teak is not big enough.
2) If you suspect that these are anchor blocks under the deck, try slowly drilling a smaller hole through the deck and look for wood shavings on your drill bit.
3) Steaming the teak, clamping it, and then screwing it may solve your problems.

as mentioned above you must first drill the teak larger than the outside diameter of the screw threads. Actually, you should be using a screw with an unthreaded shank that is as long as the thickness of teak it must go through. If there are ANY threads in the teak, then there is no actual clamping force. The pieces may be screwed together, but they are not clamped with any force beyond what the teak will deform around the threads.
The second thing you must do is make certain you drill pilot holes in the deck that are the exact diameter of the screw shaft and at least as deep as the screw needs to penetrate.
It sounds like your screws are bottoming out in the hole in the deck and then the threads in the teak are "screwing" the teak up. The gap produced is likely the additional depth you need for the pilot holes.Fiberglass is not an ideal material to thread screws into, which is why deck hardware should always be through bolted. If the pilot hole is the least bit too small, the shaft of the screw will exert enough force to crack the resin, and then the screw will loosen. Regular movement of the hardware or hull will also cause the screw to work and eventually wallow out the hole.
You may want to cut out a section of you inner liner just to see what you are really dealing with. You can always fabricate some kind of cover or repair later. Out of teak, perhaps...You can also try running in one of your screws without the teak and see what happens.
Good luck! Just think how pretty she'll be all dressed up! And remember next time if it's working leave well enough alone! lol

You asked "What makes something flush pull away from the surface you are drilling (screwing?) into?" Sounds like your pilot holes in the toe-rail material are too small. When the screw starts to bight into the sub-straight (deck) the new teak screws itself up the shaft of the fastener (the screw) at the same rate as the screw tip bights into the deck and hull flange leaving a gap. The pilot hole should be large enough and smoothly drilled to allow the fastener slid thru easily without grabbing the teak.

Screws should not be used for this application anyway, especially if the teak toe-rail is to support a genoa track or similar hard point. A toe-rail should be thru-bolted (not screwed )completely thru the toe-rail material, deck and hull flange with the proper diameter and length of SS machine screws. The bolt heads should be counter sunk and finished with teak plugs. Place all this with an ample layer of bedding compound and back it all up with large washers or backing plates and, of course, with well and evenly torqued nuts.

Man you folks are great! a couple of things that might help clear the picture. The new teak ones AND the crap fake wood are both screwed in FROM THE TOP OF THE RAIL DOWN INTO THE DECK. Screw heads will be covered with bungs then epoxied then varnished if I ever get that far.

Even though I predrilled the rails, I get what some of you are saying about the bight into the teak being what is pulling it back rather than the entry into the deck. POSITIVE and will try.

Yes I've drilled other spots, and I just don't think there is anything under there below there in which to screw into. NEGATIVE.

I didn't think about drilling again in the exact spots. I can locate them so I'll try that next to see if there is backing there. POSSIBLY a POSITIVE.

I can enlist some help to put weight on there to see if that helps. I have yet to figure out how to clamp because that would be great.

Thanks again and keep it coming if you have more to add. I'll take a pic tonight and then post it.

I don't see what you mean by the toe rail RISING 1/2". Unless you mean that the rail first goes down to the deck, then tears the screw out of the hull moulding and rises the half inch.

You have TWO bends to deal with: One is the horizontal bend that follows the gunnel in plan view, and the other is the curve in the vertical plane that is required to conform the rail to the sheer. The horizontal bend is not a problem for the screws since they will be in sheer, and even a #10 every six inches will be strong enuff to take that. The vertical bend is the problem because the screws will be in tension. But even so, #10s spaced six inches will be strong enuff to take that tension.

However, the deck moulding may NOT be able to take it! A screw of such small diameter is likely to have too little contact within the hull moulding twixt its own thread surface and that it will cut in the fibreglass. The tension of the teak is likely to tear the screw right out of the fibreglass. The original "faux wood" probably was moulded to shape and imparted NO tension.

Using the old rails as a template for spacing the holes in the new teak rail is most unlikety to result in the holes in the new teak aligning with the holes in the hull. You will be better off IMO by filling those holes in the hull by the standard method and then drilling new holes through new rail and hull while the new rail is being held temporarily in place.

Wood screws and/or "self-tappers" are not satisfactory for this job. Through bolts are required. Since you have a liner, a special technique is required that involves creating a "plug" of hard material to take the upthrust of the bolt and diffuse that thrust into the deck moulding. This "plug" needs to fill the space between hull and liner so you can get a nut on the underside of the liner. but now you will have the problem, possibly, that the holes are so close to the side of the ship that the bolts will go down twixt the liner side of the hull's side and the "back side", the hull side of the liner.

It is very common when you have to deal with the fasteners for toe rails and rubbing strapes in any yot that you have to use dynamite to get in behind the furniture to do the job. Each job needs evaluating on its own merits and each job needs to have a strategy developed BEFORE work begins.

We might be able to help you better if you can give us some pictures of what, precisely it is you mean by the rail rising the half inch.

I assumed your screws were going through the toe rail and down into the deck. What carl is describing sounds like his toe rail was screwed through holes in the inner liner then the deck and then upward into the teak. That's a potentially neater way to do it and leaves no fastener visible in the toe rail.

Trentepieds has a good point. Depending on just how big those teak pieces are, they may be exerting enough force trying to return to their natural shape to be pulling your screws out. Teak can be tortured into shapes you would never think possible, but it takes significant force to do it. And it wants to spring back into it's original shape. And depending on your hull shape you not only have to bend the teak, but you must also twist it. Depending on the shear of the deck, it must turn in and also up. In that case, you may need bigger screws to exert enough force to pull it down without tearing out the hole. Bigger screw equals bigger threads equals more force.

Through drilled bolts, nuts and backing plates will give more clamping force but do add more leak paths to seal.

I disagree -- screws may not leak into the cabin, but they could leak into the wood they are fastened into -- not good. Better to be able to see a leak if there is one.

Using bolts (with backing plates) will allow the force you need to force down the toerail onto the deck. Also less chance of stripping the screw-heads. Also allows you to use butyl, which is permanent, as you know.

Drill your holes for the teak,whilst it is bent, not when straight. Need to clamp in place, start at one end and bend and fasten as you go.
so the fastenings are going through round holes, not squashed elliptical ones

Lovely little boat! She'll give you much pleasure and she'll teach you much. She's already started doing that ;-0)! But don't worry - most of us "have seen the elephant".

Help us to help you: Give us the "moulded and sided" dimensions of the rail you are working on, i.e. the height and the thickness, because that will speak to the force you need to apply to bend it, and consequently to the "straightening" force the frozen snot of the hull and the fastenings have to resist.

Give us the specification of the screws you are using. Tell us what you are using to "bore for", i.e. make holes for the screws. Tell us what you are proposing to do to prevent ingress of water under the new rail.

When we've had a look at that, I'll see it I can draw you up a quick'n'dirty sketch of how to get the job done.

yes you need more power than just screws . Nuts and Bolts 3/8 hole 3/4 thru rail than a bolt thru the teak and hull washer buytal tape and nut every 8-10 inches. When done bung all the holes in the rail !

Man you folks are awesome! I can't thank you enough! I've done so much to her already and it's gone relatively smooth but this has been beyond me. Please look at the attached pics. The first shows a good view from above of the deck. This was the fake wood before removal.(That **** is starting to look better & better!)On getting the "for and aft bend", I weighted the pieces and put them in a pond for a month. Then they spent a month clamped to the old rails I had screwed into along board. I was surprised they sprung back to close to straight, however they seemed to have been much more easily "fastened to shape" after, it's just I had the backing out issue. These pics are the first one installed, and honestly with them as sturdy as they seem plus I've already ordered teak colored LifeCaulk, so I was going to caulk heck out of them and see how they looked. The problem is the Port side was way worse that this. I didn't get a pic of that because it was totally impractical and unsafe, and I've already taken it off and epoxied the holes.

You have one pic showing a cross section of the fake wood, showing how little of the screw went into the deck, and how much they were countersunk. I did the new teak the same way, but as a few earlier suggestions have said, maybe I drill the new rails out a bit more. These rails are planed to 3/8"and are 2.5" tall. screws are 2.5" #8 flathead stainless.

I'll take any additional advice and I can get, and I'm happy to take more pics if anyone needs to see something else.

Well, I know how to screw things up but not so much screwing them down.. But it sounds like the screw it's stopping it's progress into the fiberglass while you are still turning it to say it. That will back there teak up the shaft of the screw. Try a shorter screw, if that will provide enough holding power.